Base-promoted direct -selective olefination of organoammonium salts with sulfones toward stilbenes and conjugated 1,3-dienes

A base-promoted direct deaminative olefination of organoammonium salts was developed. Only mediated by KO t Bu, a series of benzyl and cinnamyl ammonium salts reacted smoothly with sulfones, producing the valuable stilbenes and related 1,3-diene derivatives in good to high yields with good functiona...

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Published inOrganic & biomolecular chemistry Vol. 2; no. 21; pp. 4369 - 4375
Main Authors Zhang, Tao, Wang, Runji, Chen, Jiani, Liu, Long, Huang, Tianzeng, Li, Chunya, Tang, Zhi, Chen, Tieqiao
Format Journal Article
Published 01.06.2022
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Abstract A base-promoted direct deaminative olefination of organoammonium salts was developed. Only mediated by KO t Bu, a series of benzyl and cinnamyl ammonium salts reacted smoothly with sulfones, producing the valuable stilbenes and related 1,3-diene derivatives in good to high yields with good functional group tolerance and excellent E -selectivity. With this developed method, biologically active resveratrol and DMU-212 were also successfully prepared, which further demonstrates the practicality of this reaction. A base-promoted direct deaminative olefination of organoammonium salts was developed.
AbstractList A base-promoted direct deaminative olefination of organoammonium salts was developed. Only mediated by KO t Bu, a series of benzyl and cinnamyl ammonium salts reacted smoothly with sulfones, producing the valuable stilbenes and related 1,3-diene derivatives in good to high yields with good functional group tolerance and excellent E -selectivity. With this developed method, biologically active resveratrol and DMU-212 were also successfully prepared, which further demonstrates the practicality of this reaction. A base-promoted direct deaminative olefination of organoammonium salts was developed.
Author Chen, Tieqiao
Tang, Zhi
Wang, Runji
Chen, Jiani
Li, Chunya
Liu, Long
Huang, Tianzeng
Zhang, Tao
AuthorAffiliation Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources
Hainan Provincial Key Lab of Fine Chem
Hainan University
Hainan Provincial Fine Chemical Engineering Research Center
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